20 Shockingly Bad Investments That Crashed and Burned

Everyone dreams of making that one investment that turns into a goldmine. However, for every success story, dozens of spectacular flops leave investors wishing they had just kept their money under the mattress instead.

From overhyped startups to doomed products and disastrous business decisions, history is littered with financial faceplants. Let’s take a look at 20 shockingly bad investments that crashed and burned epically.

20. Pets.com

Once hailed as the future of pet supply shopping, Pets.com quickly became a symbol of the dot-com disaster. Despite a Super Bowl ad and a famous sock puppet mascot, the company went belly up in less than a year.

19. MoviePass

The idea of unlimited movies for one low price sounded too good to be true—and it was. MoviePass burned through cash faster than you could say “box office bomb,” and eventually collapsed under its weight.

18. Theranos

Investors thought they were funding a revolutionary blood-testing company, but instead, they backed a masterclass in corporate deception. Theranos’ downfall became one of the most infamous investment debacles in modern history.

17. Juicero

Juicero raised millions for a high-tech juicer that turned out to be completely unnecessary. When people realized you could squeeze the juice packs with your hands, the company became a $120 million punchline.

16. Beanie Babies

For a hot second, Beanie Babies looked like a ticket to untold riches. Then the bubble burst, leaving collectors—and investors—stuck with mountains of adorable but worthless stuffed animals.

15. Quibi

Quibi promised to revolutionize short-form entertainment, but forgot to make anything people wanted to watch. After burning through nearly $2 billion, the app shut down faster than a skipped YouTube ad.

14. DeLorean Motor Company

The DeLorean car looked cool enough to star in Back to the Future, but the company behind it was a complete financial wreck. Mismanagement, legal troubles, and poor timing all contributed to driving this investment straight off a cliff.

13. Segway

Segway was supposed to be the future of personal transportation, but it ultimately became the future of mall security guards. Despite all the hype, consumers were not willing to shell out big bucks to look like futuristic tourists.

12. MySpace

Before Facebook ruled the world, there was MySpace—and it could have stayed on top with the right moves. Instead, it became a cautionary tale of bad management, missed opportunities, and profiles glittered into oblivion.

11. Blockbuster’s Netflix Snub

Blockbuster famously passed on the chance to buy Netflix for $50 million. Now, Blockbuster is a trivia question, and Netflix is a multi-billion-dollar global powerhouse.

10. Kodak’s Digital Blindness

Kodak invented the digital camera but refused to embrace it, fearing it would cannibalize their film business. That decision buried a once-dominant brand under a mountain of missed opportunities.

9. WeWork

WeWork was supposed to be the future of coworking, but it turned into the future of throwing away billions. Lavish spending, a questionable business model, and a cartoonishly over-the-top CEO all contributed to the crash.

8. Enron

At one point, Enron was considered a darling of Wall Street. Then it turned out they were cooking the books so badly that the entire company imploded in a scandal that still makes business schools wince.

7. RadioShack

Once the go-to spot for electronics, RadioShack failed spectacularly to adapt to the modern tech world. It’s now a cautionary tale of what happens when you think people still want to buy batteries at the mall.

6. BlackBerry

BlackBerry dominated the smartphone market before smartphones became mainstream. Then Apple and Android emerged, and BlackBerry slowly slipped into irrelevance, hanging on longer than anyone expected.

5. JCPenney’s Rebranding Fiasco

JCPenney decided it didn’t need coupons, sales, or anything its customers liked. The rebranding effort failed so badly that it sent the company into a downward spiral from which it has never fully recovered.

4. Sears’ Slow Demise

Once the king of American retail, Sears managed to fumble its way into irrelevance due to poor leadership and a lack of clear strategy. It turns out you can’t just coast forever on a good catalog.

3. Fyre Festival

Investors thought they were backing the next Coachella but ended up funding the world’s most luxurious disaster. The Fyre Festival is now infamous for sad cheese sandwiches and broken dreams.

Read More: 30 Companies That Lost Money in Shockingly Stupid Ways

2. Yahoo’s Missed Opportunities

Yahoo had multiple opportunities to acquire Google and Facebook, but passed on them. Now, Yahoo is mainly remembered as that old email account you forgot the password to.

Read More: 10 Weird Business Ideas That Made a Fortune

1. Toys “R” Us Private Equity Takeover

Private equity firms saddled Toys “R” Us with so much debt that even Geoffrey the Giraffe couldn’t carry it. The beloved toy store chain eventually collapsed under the financial burden, leaving a generation of children—and investors—heartbroken.

Read More: 10 Brands That Used To Be Great—But Lost Their Value